Chemoselective sequential click ligations directed by enhanced reactivity of an aromatic ynamine
Hatit, Marine Z. C. and Sadler, Joanna C. and McLean, Liam A. and Whitehurst, Benjamin C. and Seath, Ciaran P. and Humphreys, Luke D. and Young, Robert J. and Watson, Allan J. B. and Burley, Glenn A. (2016) Chemoselective sequential click ligations directed by enhanced reactivity of an aromatic ynamine. Organic Letters, 18 (7). pp. 1694-1697. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.6b00635)
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Abstract
Aromatic ynamines or N-alkynylheteroarenes are highly reactive alkyne components in Cu-catalyzed Huisgen [3 +2] cycloaddition (“click”) reactions. This enhanced reactivity enables the chemoselective formation of 1,4-triazoles using the representative aromatic ynamine N-ethynylbenzimidazole in the presence of a competing aliphatic alkyne substrate. The unique chemoselectivity profile of N-ethynylbenzimidazole is further demonstrated by the sequential click ligation of a series of highly functionalized azides using a heterobifunctional diyne, dispelling the need for alkyne protecting groups.
ORCID iDs
Hatit, Marine Z. C. ORCID: https://orcid.org/0000-0002-5713-6596, Sadler, Joanna C. ORCID: https://orcid.org/0000-0002-8442-0760, McLean, Liam A. ORCID: https://orcid.org/0000-0002-1862-8619, Whitehurst, Benjamin C., Seath, Ciaran P. ORCID: https://orcid.org/0000-0002-6774-128X, Humphreys, Luke D., Young, Robert J., Watson, Allan J. B. and Burley, Glenn A.;-
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Item type: Article ID code: 56054 Dates: DateEvent1 April 2016Published22 March 2016Published Online22 March 2016AcceptedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry
Technology and Innovation Centre > BionanotechnologyDepositing user: Pure Administrator Date deposited: 31 Mar 2016 13:03 Last modified: 20 Nov 2024 01:12 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/56054